Products and Mechanisms in the Anodic Oxidation of Solanidine-Type Steroidal Alkaloids

Autor:	E. Gunic, Dušan Miljković, I. Juranic, Ibro Tabakovic, K. M. Gasi
Rok vydání:	1994
Předmět:	chemistry.chemical_compound Perchlorate chemistry Transition metal Yield (chemistry) Organic Chemistry chemistry.chemical_element Regioselectivity Electrolyte Electrochemistry Platinum Medicinal chemistry Solanidine
Zdroj:	The Journal of Organic Chemistry. 59:1264-1269
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00085a011
Popis:	Anodic oxidation of Δ 4 -solaniden-3-one, 2, 3β-acetoxysolanidin, 5, and 3β-acetosy-5α-chlorosolanidin, 6, were performed in CH 3 CN-CH 2 Cl 2 (1:1)-tetraethylammonium perchlorate electrolyte solution at platinum using controlled potentials. As a result of two-electron oxidation the corresponding N-22 immonium salts (2a, 5a, and 6a) and N-16 immonium salts (2b, 5b, and 6b) were in good yield (75-82%) with a ratio of a/b products of approximately 1-1. The effect of solution conditions on regioselectivity, e.g., formation of 2a and 2b, has been shown to be remarkable
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e3f25fc57db6daf9aa9fab5de4d591e8 https://doi.org/10.1021/jo00085a011 Zobrazit plný text záznamu